3,3'-Bis(trifluoromethyl)benzophenone → bis[3-(trifluoromethyl)phenyl]methanol

HRID 1027458Notes

Reaction equation

HRID 1027458 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:7].[BH4-].[Na+]>CO.O>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[C:5]([CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)[OH:7])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 5997883,3'-Bis(trifluoromethyl)benzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 2736113bis[3-(trifluoromethyl)phenyl]methanolYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3,3′-bis(trifluoromethyl)benzophenone (11.4 g, 36 mmol) in MeOH (50 mL) was added sodium borohydride (1.9 ml, 53 mmol) portionwise at rt. The suspension was stirred at rt for 24 h. The reaction was diluted slowly with water and extracted with CH2Cl2. The organic was washed successively with water, brine, dried over Na2SO4, and concentrated to give bis(3-(trifluoromethyl)phenyl)methanol (10.8 g, 94% yield). The crude oil was used in the next reaction without further purification.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic was washed successively with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5898359ff49a474bb2c8b1833a61239e
Source dataset
uspto-grants-2014_05
Patent number
US08735383B2

Reaction notes

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